Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o‐Alkynylaryl Weinreb Amides

[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride‐induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were converted into difluoromethyl ketones through selective reductive c...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-12, Vol.2017 (46), p.6840-6850
Main Authors: Phetcharawetch, Jongkonporn, Betterley, Nolan M., Soorukram, Darunee, Pohmakotr, Manat, Reutrakul, Vichai, Kuhakarn, Chutima
Format: Article
Language:English
Subjects:
Amides
Benzoic acid
Carbonyl groups
Carbonyls
Fluorinated compounds
Fluorine
Ketones
Nucleophilic substitution
Tandem reaction
Weinreb amides
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Summary:[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride‐induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were converted into difluoromethyl ketones through selective reductive cleavage of the phenylsulfanyl group. The reaction of o‐alkynyl Weinreb amides derived from benzoic acid derivatives resulted in the formation of cyclized products through a 5‐exo‐dig cyclization. The synthesis of difluoromethyl ketones was accomplished through a fluoride‐induced nucleophilic substitution reaction of PhSCF2SiMe3 with Weinreb amides followed by a chemoselective reductive desulfurization using Raney nickel and H2.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701322